4-4-difluoro-4-bora-3a-4a-diaza-s-indacene and morpholine

A small series of fluorescent lysosome-targeting probes based on the BODIPY fluorophore and containing morpholine and nitro groups were rationally designed. These probes emitted light from green to NIR wavelengths, and provided specificity for imaging the lysosomes of hypoxic cells. The electron-withdrawing nitrophenyl group at the meso position was found to lead to highly efficient nonradiative decay of the S1 state, and hence a recovery of fluorescence when reduction of the nitro group occurred under hypoxic conditions.

Topics: Boron Compounds; Cell Hypoxia; Density Functional Theory; Fluorescent Dyes; Hep G2 Cells; Humans; Light; Lysosomes; Morpholines; Spectrometry, Fluorescence

A highly efficient direct C-H amination of BODIPYs has been accomplished through the Ag(i)-mediated nucleophilic addition of an amino radical to BODIPY at the C3- and/or C5-position and deprotonation processes under mild conditions. This protocol greatly streamlines the access to a variety of 3-aminated and 3,5-diaminated BODIPYs. The resulting BODIPYs with morpholine groups (3q and 4b) exhibit specific endoplasmic reticulum (ER)-localization capacities and negligible cytotoxicities, which would be potential ER-targeting reagents.

Topics: Amination; Boron Compounds; Carbon; Endoplasmic Reticulum; Fluorescent Dyes; Hep G2 Cells; Humans; Hydrogen; Microscopy, Fluorescence; Morpholines; Silver